Two Weeks in Portugal and the Azores Itinerary
- Brooke
- Jul 27, 2023
- 6 min read
Updated: Jul 30, 2023

(This post is an itinerary post to help those looking for advice on how to spend their time in certain locations. For more detailed information about the destinations, look for postings about the individual places listed below. See the Trips page for more information).
In the late spring of 2018, Ben and I joined his family in Portugal for a fun adventure. While we spent a few days in Lisbon at the beginning and Porto at the tail end, the majority of our time was spent in the Azores, a scenic volcanic island chain in the middle of the Atlantic Ocean. Two hours away from the Portuguese mainland, it has a distinct character that was reminiscent of Hawai‘i, and yet still decidedly Portuguese. We absolutely loved our time there, and look forward to visiting again someday soon to Portugal and the Azores.
Itinerary
Day 1: May 2nd, 2018
Depart Atlanta for New York City and Lisbon
Because Ben had a work function in Atlanta for a few days before our trip, we had the unusual (for us) experience of departing from Europe from Georgia instead of Hawaii, or the Northeast. We flew from ATL to JFK and had a bit of a long layover there; however, there is a lounge that you can pay to access in the area near TAP's gate that we took advantage of.
Day 2: May 3rd, 2018
Arrive Lisbon
Depart: New York City 11:25 PM on TAP Airlines
Arrive: Lisbon 11:15 AM
Stay: Castle View Apartment Lisbon AirBnB
The view was incredible, and the apartment was spacious, clean and great for Ben and I and his parents. Would definitely stay here again - super easy to get to and from everything, and its location in Martim Moniz Square made it easy for taxi drivers to know how to get you home.

Dinner: Restaurante Clube de Journalistas
Very cute restaurant that served delicious food. The chef/manager even gave us a free fabric tote bag at the end of the meal, as well as some canned sardines (?), and I think I love them for it?

Day 3: May 4th, 2018
Explore Lisbon
Activity: Culinary Backstreets Lisbon Food Tour, which started at the Time Out Market
The tour we took is no longer offered, but we loved every moment of it, and would highly recommend their other offerings because we enjoyed our experience so much.

Activity: Sunset Sail on Tagus River
A really lovely way to see the city, if not a little confusing finding the boat. Still, once aboard, we have a great time.

Day 4: May 5th, 2018
Explore Lisbon
Activity: Wander around the St. George Castle (Castelo de São Jorge) and environs (but leave my fancy camera in the apartment!!!)


After coming down the hill, Ben and I went and did a little more exploring on our own.

Because we had sampled Ginja during the food tour, we were on a mission to grab a bottle for ourselves. We purchased the Espinheira bottle, and it was delicious!
Dinner: Fado Performance at Parreirinha de Alfama
A beautiful evening of guitar and singing, as well as a delicious meal. They say it's a don't miss while in Lisbon, and I agree!
Day 5: May 6th, 2018
Depart Lisbon for Azores
Depart: Lisbon 11:00AM on TAP Airlines

Arrive: Ponta Delgada 12:25PM


This hotel was truly incredible - our room was super spacious, and the location simply can't be beat. Highly, highly recommend!
Dinner: Restaurant (within hotel)
Day 6: May 7th, 2018
Exploring São Miguel
Activity: Explore Sete Cidades

On some days, the two lakes, separated by a small isthmus, are different colors (the larger one appears blue while the smaller one appears green). It wasn't so obvious on the day we visited, though if you squint your eyes just so...
Visit: Ceramica Vieira in Lagoa

Visit: Praia do Areal de Santa Bárbara (in front of hotel)

Dinner: Alcides Restaurante in Ponta Delgada

Day 7: May 8th, 2018
Exploring São Miguel
Activity: Whale Watch with Sea Colors

A fun adventure out on the ocean looking for sea life. We had the incredible experience of being followed by dolphins, and got to see a grey whale, a first for yours truly. As seen above, we also spotted a humpback - something we've seen a bunch in Hawai‘i, but still no less magical on this side of the world.
Lunch: Café Central in Ponta Delgada

Dinner: TukáTulá Beach Bar in Ribeira Grande

Day 8: May 9th, 2018
Exploring São Miguel
Activity: Day trip to Furnas and Drive Around Island
Furnas is an interesting town full of volcanic activity. Ben and I came here this first day by ourselves, but returned for a second day with Ben's family. I've read that itineraries recommend spending two nights here, and I would also second this - there really is enough to do in this corner of the island, and it's very charming and fun to see.
Explore: Terra Nostra Gardens

Explore: Caldeiras of Furnas

Lunch: Restaurante Caldeiras e Vulcões for the traditional Cozido Das Furnas

Explore: The rest of the island, including stops in:
Ribeira Quente

Miradouro do Ramalho

Miradouro do Ponta da Madrugada

Dinner: Quinta dos Sabores

All of the food in the Azores (and indeed, Portugal on a whole) was delicious, but this place was my favorite. There is no set menu, they simply serve everyone what they feel like making that day, using local produce that they either grow or access from local farmers, and then there you have it. At the time I didn't have a myriad of dietary restrictions, but I was glad to read that they are quite accommodating to all sorts of allergies and preferences. I would be thrilled to dine here again.
Day 9: May 10th, 2018
Exploring São Miguel
Activity: Another day trip to Furnas and drive around island, but this time with Ben's family
Explore: Terra Nostra Garden

Explore: Fumarolas Lagoa das Furnas and Mata Jardim José do Canto
Lunch: Restaurante TN within Terra Nostra Garden Hotel

Activity: Poça da Dona Beija

Blog Post: Taking a Relaxing Dip in Poça da Dona Beija
Explore: Miradouro de Santa Iria


Day 10: May 11th, 2018
Exploring São Miguel

Activity: Shopping in Ponta Delgada and Elsewhere
Stops included:




Explore: Chá Gorreana Tea Factory
Dinner: Restaurante O Silva (Ribeira Grande)

Day 11: May 12th, 2018
Departing Azores for Sintra and Porto
Depart: Ponta Delgada 7:00 AM on TAP Airlines
Arrive: Lisbon 10:10 AM
After arriving, we headed straight to the car rental agency - and proceeded to wait for at least an hour to get a car. If possible, sign up for your car rental's quicker service to avoid long lines - it's worth it!
Explore: Regional de Colares Winery

Lunch: Restaurante da Várzea

Explore: Park and Palace of Monserrate

Stay: Airbnb in Porto. I can no longer find this unit on the page, but there are lots of great options around the city.




A truly magical dining experience in an incredible setting. Worth the effort to get here - we'll always remember it!
Day 12: May 13th, 2018
Boat Trip from Porto up the Douro River
Activity: Full day boat trip up Douro River using Cruzeiros Douro with train ride back to Porto from Régua.
Depart: Estiva Quay 8:45 AM

A long, full day of cruising the Douro River. This is not the most scenic part of the river, though it's certainly charming in its own right. I only recommend this excursion if you are *also* doing exploration further up the river, like we did.





Régua Arrival


Arrive: Porto 7:15 PM

Dinner: Estambul Döner Kebap

Day 13: May 14th, 2018
Explore Porto
We used this day as a day to relax, catch up on work, and do some laundry, while doing some light sightseeing by walking around the city.
Breakfast: Confeitaria São Domingos

Lunch: El Argento

Shopping: Ó! Galleria


Dinner: Rui Paula's DOP Restaurant


Rui Paula has a slight monopoly on fine dining in and around Porto, and for good reason.
Day 14: May 15th, 2018
Day Trip Into the Douro Valley
Activity: Full day excursion with Bruno Simões at Douro Vintage Tours
(This is honestly one of our most memorable excursions ever - highly recommend!)

Depart: Porto at 8:15 AM (picked up by Bruno)
Activities included:
Olive oil and wine tasting at D'Origem

Rabelo Boat trip: Pinhão - Roncão and back

Private lunch at Casa Típica Papas Zaide

Perhaps one of the best meals on the whole trip? This restaurant, from what I can tell, does not accept walk-ins. Do yourself a favor and make a reservation, and then enjoy the traditional flavors of Portugal cooked with love and care.

Port tasting at Quinta do Bomfim

Wine tasting at Quinta do Pôpa

Arrive: Porto 7:00 PM (dropped off at our apartment)
Dinner: Belos Aires Restaurante

Day 15: May 16th, 2018
Depart Portugal for Amsterdam
Depart: Porto 5:00 AM on KLM Airlines
Arrive: Amsterdam 8:40 AM
Well, it was time to head off on our next portion of the trip - Amsterdam! Ben and I would spend a few days there, before he would depart for Hawaii. I would wait a while longer to meet up with my mother for our Baltic Cruise. Meanwhile, the Portugal portion of the trip lived up to the hype and more. If you get a chance to head there, I hope you'll use this itinerary as an opportunity to see all that this lovely country has to offer.
*See post for the Netherlands Itinerary - see you there!
Comments